Echinocystic acid

Base Information

• Chemical Name: Echinocystic acid
• CAS No.: 510-30-5
• Molecular Formula: C30H48 O4
• Molecular Weight: 472.709
• European Community (EC) Number: 208-112-3
• UNII: L4DUW10YOF
• DSSTox Substance ID: DTXSID70965278
• Nikkaji Number: J14.013I
• Wikidata: Q27106464
• Pharos Ligand ID: SSSM2T4SMPHG
• ChEMBL ID: CHEMBL230128
• Mol file: 510-30-5.mol

Synonyms:echinocystic acid

Chemical Property of Echinocystic acid

Chemical Property:

• Melting Point: 299-300°C
• Boiling Point: 585°Cat760mmHg
• PKA: 4.43±0.70(Predicted)
• Flash Point: 321.6°C
• PSA: 77.76000
• Density: 1.14g/cm³
• LogP: 6.20440
• Storage Temp.: 2-8°C
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 919

Purity/Quality:

98% ^*data from raw suppliers

Echinocystic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)O)C)C(=O)O)C
• Isomeric SMILES: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)O)C)C)(C)C)O
• Description: Echinocystic acid is a triterpene that has been found in G. sinensis and has diverse biological activities. It induces nuclear translocation of the glucocorticoid receptor (GR) and reduces TNF-α-induced NF-κB signaling in HEK293 cells overexpressing GFP-GR. Echinocystic acid (12.5, 25, and 50 μM) suppresses RANKL-induced NF-κB activation, ERK phosphorylation, and osteoclastogenesis in mouse bone marrow macrophages (BMMs). It induces neurite outgrowth in Neuro2A cells in a concentration-dependent manner, an effect that can be blocked by the JNK inhibitor SP 600125 . In vivo, echinocystic acid (10 mg/kg per day) decreases escape latency in the Morris water maze and increases the length of neurite processes in the hippocampus of aged mice. Topical administration of echinocystic acid reduces expression of COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β and ear edema induced by phorbol 12-myristate 13-acetate (TPA; ) in a mouse model of dermatitis. Echinocystic acid also recovers reductions in femoral bone mineral density and trabecular thickness and number in a rat model of ovariectomy-induced osteoporosis.
• Uses: Echinocystic Acid is a potential entry inhibitor for the HCV infection.

Technology Process of Echinocystic acid

There total 58 articles about Echinocystic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-{β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-[2-O-cinnamoyl-α-L-arabinopyranosyl-(1→4)]-6-O-acetyl-β-D-glucopyranosyl} ester → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + echinocystic acid (510-30-5)

Guidance literature:

With hydrogenchloride; water; at 85 ℃; for 2h;

DOI:10.1016/j.phytol.2017.09.008

Reference yield:

3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-(β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-{2-O-[(6S,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-α-L-arabinopyranosyl-(1→4)}-6-O-acetyl-β-D-glucopyranosyl) ester → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + echinocystic acid (510-30-5)

Guidance literature:

With hydrogenchloride; water; at 85 ℃; for 2h;

DOI:10.1016/j.phytol.2017.09.008

Reference yield:

3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-(β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-{2-O-[(6S,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl-3-O-cinnamoyl]-α-L-arabinopyranosyl-(1→4)}-6-O-acetyl-β-D-glucopyranosyl) ester → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + echinocystic acid (510-30-5)

Guidance literature:

With hydrogenchloride; water; at 85 ℃; for 2h;

DOI:10.1016/j.phytol.2017.09.008

upstream raw materials:

tragopogonoside A methyl ester

echinocystic acid 3-O-β-D-xylopyranosyl-(1->2)-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside

Downstream raw materials:

primulagenin A

2,7-dimethylnaphthalene

1,2,3,4-Tetramethylbenzene

1,2,5,6-tetramethylnaphthalene

Refernces

• 1、 Nakamura,Takeda,Ogihara. "Studies on the constituents of Calliandra anomala (KUNTH) MACBR. II. Structure elucidation of four acylated triterpenoidal saponins". . p. 1111 - 1115. Retrieved 1994.
• 2、 Li, Jian-Ping,Liang, Zhi-Min,Yuan, Zhong. "Triterpenoid saponins and anti-inflammatory activity of Codonopsis lanceolata". . p. 463 - 466. Retrieved 2007.
• 3、 Komoto, Noriko,Ichikawa, Makoto,Ohta, Sanae,Nakano, Daisuke,Nishihama, Takeshi,Ushijima, Mitsuyasu,Kodera, Yukihiro,Hayama, Minoru,Shirota, Osamu,Sekita, Setsuko,Kuroyanagi, Masanori. "Murine metabolism and absorption of lancemaside A, an active compound in the roots of Codonopsis lanceolata". . p. 321 - 329. Retrieved 2010.
• 4、 Tchoukoua, Abdou,Kuiate Tabopda, Turibio,Konga Simo, Ingrid,Uesugi, Shota,Ohno, Misa,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu. "Albidosides H and I, two new triterpene saponins from the barks of Acacia albida Del. (Mimosaceae)". . p. 924 - 932. Retrieved 2018/02/15.
• 5、 Tchoukoua, Abdou,Tabopda, Turibio Kuiate,Usukhbayar, Narandulam,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Koseki, Takuya,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu. "New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)". . p. 2261 - 2267. Retrieved 2017/12/26.